METHOD OF PRODUCING A DIAZABICYCLOOCTANE DERIVATIVE AND INTERMEDIATE THEREOF Russian patent published in 2020 - IPC C07D471/08 C07D401/12 

FIELD: organic chemistry.

SUBSTANCE: invention relates to a method of producing a diazabicyclooctane derivative of formula (IV), involving reacting a compound of formula (I) with R¹ OH selected from 1-hydroxypyrrolidine-2,5-dione, 2-hydroxy-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione, 2-hydroxyhexahydro-1H-isoindole-1,3(2H)-dione and 4-hydroxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione, to give a compound of formula (II), wherein R² represents hydrogen, OBn, P and R¹ are such as described below, followed by carbonylation with a carbonylating agent selected from phosgene, diphosgene and triphosgene to obtain a compound of formula (II), where R² is ClCO- or Cl₃COCO-, OBn, P and R¹ are as described below, removal of the protective group P and treatment with a base to obtain a compound represented by the following formula (III), and reacting with compound R³ONH₂ to obtain a compound of formula (IV), where OBn is benzyloxy, P is an NH-protective group deleted by an acid, R¹ is 2,5-dioxopyrrolidin-1-yl, 1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-yl, 1,3-dioxohexahydro-1H-isoindole-2(3H)-yl or 3,5-dioxo-4-azatricyclo [5.2.1.0^2.6]dec-8-en-4-yl, R³ is selected from 2-(tert-butoxycarbonylamino)ethyl; 2-((tert-butoxycarbonyl)(methyl)amino)ethyl; 3-((tert-butoxycarbonyl)amino)propyl; (2S)-tert-butoxycarbonylazetidin-2-ylmethyl; (3S)-tert-butoxycarbonylpyrrolidin-3-yl; 1-(tert-butoxycarbonyl)azetidin-3-ylmethyl; 2-(benzyloxycarbonylamino) ethyl. Invention also relates to specific intermediate compounds obtained during synthesis of the compound of formula (IV).

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EFFECT: method of producing a diazabicyclooctane derivative of formula (IV), characterized by high output of the desired compound.

23 cl, 93 ex